The absolute stereochemistry of micropeptin 90

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9225-9226

  Ishida, Keishi ^a   Matsuda, Hisashi ^a   Murakami, Masahiro ^a   Yamaguchi, Katsumi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DEPSIPEPTIDE;

ARTICLE; CYANOBACTERIUM; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

MICROCYSTIS AERUGINOSA;

EID: 0030590973     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02189-2     Document Type: Article

References (13)

1. 1. Ishida, K.; Murakami, M.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 3535-3538.
2. 2. a) Harada, K-I.; Mayumi, T.; Shimada, T.; Suzuki, M.; Kondo, F.; Watanabe, M. F. Tetrahedron Lett. 1993, 34, 6091-6094.
3. b) Tsukamoto, S.; Painuly, P.; Young, A.; Yang, X.; Shimizu, Y. J. Am. Chem. Soc. 1993, 115, 11046-11047.
4. c) Martin, C.; Oberer, L.; Ino, T.; König, W. A.; Busch, M.; Weckesser, J. J. Antibiot. 1993, 46, 1550-1556.
5. d) Okino, T.; Murakami, M.; Haraguchi, R.; Munekata, H.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1993, 34, 8131-8134.
6. e) Shin, H. J.; Murakami, M.; Matsuda, H.; Ishida, K.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 5235-5238.
7. f) Sano, T.; Kaya, K. J. Nat. Prod. 1996, 59, 90-92.
8. 3. Lee, A. Y.; Smitka, T. A.; Bonjouklian, R.; Clardy, J. Chemistry & Biology 1994, 1, 113-117.
9. 4. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.
10. 5. Matsunaga, S.; Fusetani, N. J. Org. Chem. 1995, 60, 1177-1181.
11. 2O/TFA (23:77:0.1); UV (340 nm). Retention times of standards (min): N-Me L-Tyr-L-FDAA (39.2), N-Me L-Tyr-D-FDAA (40.8). Retention time of N-MeTyr-L-FDAA in the acid hydrolyzate of micropeptin 90 (min): 39.2.
12. 2 and analyzed by GC with Chirasil-L-Val (Chrompak) column. The oven temperature was maintained at 40 °C for 3 min and raised to 70 °C at 4 °C/min, which was maintained for 25 min. Retention times for glyceric acids (min): D-glyceric acid (18.84), L-glyceric acid (19.07). Retention time of a derivative of the acid hydrolyzate of micropeplin 90 (min): 18.77.
13. 2O/TFA (60:40:0.1) in 60 min; UV (340 nm). Retention times of the standard amino acids (min): L-Glu (39.4), D-Glu (40.4). Retention time of a derivative derived from micropeptin 90 (min): 39.4.